8 Winning Deal Strategies
The Compass
How to Win Competitive Deals: The 8 Compass Sales Strategies for Sales Success
Introduction: Why You Need a Competitive Sales Strategy
In B2B sales today, we operate in hyper-competitive markets under rapidly changing business conditions. Our competition comes in different forms. There are direct competitors—companies that provide similar solutions. There are also indirect competitors—other initiatives and projects within the buyer’s organization competing for scarce budget and executive attention. And then there is the most formidable competitor of all: the no-decision. Many deals are lost not because another vendor won, but because the buyer chose to do nothing.
Without a clear competitive strategy, you are simply reacting to these forces rather than controlling the deal.
The Problem: Many sales professionals rely on a single approach—pushing harder, discounting deeper, or flooding prospects with more meetings. But strategy is not about effort; it’s about position & momentum.
The Solution: By mastering these 8 Compass Sales Strategies, you can anticipate, maneuver, and win against these competitive elements. It’s about controlling the deal rather than merely reacting. You’ll learn how to counter direct competitors, outmaneuver indirect competitors, and overcome the inertia of no-decision deals. These strategies are not just about force—they are about strategically managing time, velocity, and position in a deal to gain a decisive advantage.
🚀 If you don’t choose a strategy, your competition will choose one for you.
The 8 Compass Sales Strategies
Each strategy serves a specific purpose in different competitive deal scenarios. Here’s how they work:
1. Direct or Push Strategy.
💡 Concept: Maneuver or push your deal directly to a close. Nothing fancy. Don’t overthink it.
📌 Best Used When: You have a superior product, strong executive relationships, clearly defined value proposition and a compelling business event driving the timeframe for a close.
⚠️ Strategic Insight: Michael Porter states, “The essence of strategy is choosing what not to do.” A direct strategy works only if your differentiation is clear and defensible.
2. Indirect or Pull Strategy
💡 Concept: You approach the deal from a different direction than the competition. You pull the deal toward your strengths having the Buyer see their requirements from a new perspective.
📌 Best Used When: You are in a highly competitive position or when the competition is stronger but rigid, slow, or overcommitted.
⚠️ Strategic Insight: Richard Rumelt emphasizes, “Good strategy works by focusing resources and energy on one or a very few pivotal objectives.” Indirect strategies allow you to pull the competition into a game they can’t win.
3. Divisional or Split Strategy
💡 Concept: You break the deal into smaller parts. You do this by employing a land & expand strategy or win by dividing the buyer’s decision-making team so competitors struggle to maintain control.
📌 Best Used When: You are not in a position of strength to close the larger, defined opportunity or where there is internal conflict within the buyer’s organization (e.g., finance vs. operations).
⚠️ Strategic Insight: A.G. Lafley & Roger Martin argue, “Winning strategy is about making explicit choices on where and how to play.” Creating division within the buying process ensures competitors cannot maintain a united front.
4. Maneuver or Flanking Strategy
💡 Concept: Win by attacking where competitors are weakest—taking advantage of overlooked opportunities.
📌 Best Used When: The competition dominates the main requirements but ignores adjacent opportunities.
⚠️ Strategic Insight: John Boyd’s OODA Loop suggests, “The key to victory is to shape your competition’s perception faster than they can react.” Maneuver strategies exploit weaknesses before competitors can adjust.
5. Trail or Momentum Strategy
💡 Concept: Here you attach your deal to another stronger project that has funding and leveraging their groundwork. This is where partnerships can play to your advantage.
📌 Best Used When: You don’t have enough deal momentum to close the deal or risk losing to higher priority projects.
⚠️ Strategic Insight: Geoffrey Moore states, “Early adopters are willing to work with you if you fit into their vision of the future.” The Trail Strategy works best when you can seamlessly integrate into an existing trend or project.
6. Surround or Envelop Strategy
💡 Concept: Win by applying simultaneous pressure on multiple decision-makers across different levels of the organization.
📌 Best Used When: The deal involves multiple stakeholders with differing priorities.
⚠️ Strategic Insight: Lawrence Freedman highlights, “Strategy is about power and influence—control the environment, and you control the outcome.” A Surround Strategy ensures your message is dominant across all key decision-makers.
7. Challenge or Reframe Strategy
💡 Concept: You challenge the validity of the evaluation criteria as not in the best interest of the Buyer and attempt to reframe or rework the evaluation criteria into a more favorable position. You basically blow the deal up.
📌 Best Used When: You are losing the deal.
⚠️ Strategic Insight: Richard Rumelt notes, “A bad strategy is a failure to face the challenge. A good strategy works through problems.” Containment prevents competitors from gaining the momentum they need to close.
8. Attrition or Progressive Overload Strategy.
💡 Concept: Win by outlasting competitors and wearing down their resources over time. In some cases you intentionally lengthen the sales cycle to wear them out.
📌 Best Used When: The competition has a stronger offering but has weaker long-term staying power or operates in a resource-intensive model.
⚠️ Strategic Insight: A.G. Lafley & Roger Martin argue, “The most enduring advantage comes from deepening the moat.” Attrition strategies succeed when competitors can’t sustain the fight.
How to Choose the Right Strategy for Your Competitive Deals
Many sales teams default to Direct or Discounting Strategies, both of which can be losing plays. The best approach is to evaluate your competitive position before selecting a strategy on a regular basis.
✅ Use Direct when you have clear superiority.
✅ Use Indirect when the competition is stronger but predictable.
✅ Use Divisional when the buyer is already fragmented.
✅ Use Maneuver when competitors are ignoring key opportunities.
✅ Use Trail when you can attach to market momentum.
✅ Use Surround when multiple stakeholders influence the deal.
✅ Use Containment when you need to slow a competitor’s lead.
✅ Use Attrition when you can afford to outlast them.
📌 Pro Tip: The best sellers combine multiple strategies. For example, an Indirect entry can lead into a Surround Strategy before closing with a Direct push.
Closing & Call to Action
🔹 Key Takeaway: The best sales professionals win not because they work harder, but because they choose the right strategy at the right time.
🔥 Next Up in the Series:
Deep Dive into the Direct Strategy: When to Use It, When to Avoid It, and How to Execute It for Maximum Impact.
💬 Engagement:
"Which of these strategies do you find yourself using most often in sales? Drop a comment and let’s discuss!"
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Sources: Here's a partial list of some of the great strategy writers I’ve read over the years, applied to my deals and are the foundation of some of the Compass system framework. Some worked and some didn’t. But knowing what not to do is as important as knowing what to do.
Sun Tzu: "The Art of War" - Ancient military strategy
Richard P. Rumelt: "Good Strategy Bad Strategy" - Business strategy
A.G. Lafley and Roger L. Martin: "Playing to Win" - Corporate strategy
Geoffrey A. Moore: "Crossing the Chasm" - Technology strategy
Henry Mintzberg: "Strategy Safari" - Strategic management
Liddell Hart: "Strategy of Indirect Approach" - Military strategy
J.C. Spender: "Business Strategy" - Uncertainty and entrepreneurial strategy
John P. Kotter: "Accelerate" - Organizational strategy
Lawrence Freedman: "Strategy: A History" - Comprehensive strategic thinking
Clayton Christensen: Disruptive innovation strategy
Michael Porter: Corporate competitive strategy.
Another of my favorite books is “Boyd”. It is the story of John Boyd, a Korean War fighter pilot and the original Top Gun. He was never defeated in arial combat nor in the top gun school as a student and teacher. He was the creator of the OODA Loop for making fast decisions in competitive situations under rapidly conditions.
I train sales professionals, business leaders, and their AI agents on Sales and Deal strategies using the Compass AI Sales Strategy system. This training acts as a force multiplier, empowering you and your AI agents to work in alignment to win business and exceed your number in competitive environments.
This was written while listening to ‘Rose Rouge’ by St. Germain.
Artwork: Limelight Dreams By Amy Donaldson.
